Cyproheptadine (CHEM002195)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:53 UTC
Update Date2026-05-14 16:38:38 UTC
Accession NumberCHEM002195
Identification
Common NameCyproheptadine
ClassSmall Molecule
DescriptionCyproheptadine is only found in individuals that have used or taken this drug. It is a serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc. Cyproheptadine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Cyproheptadine also competes with serotonin at receptor sites in smooth muscle in the intestines and other locations. Antagonism of serotonin on the appetite center of the hypothalamus may account for Cyproheptadine's ability to stimulate appetite.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Anti-Allergic Agent
  • Antihistamine Derivative
  • Antipruritic
  • Drug
  • Food Toxin
  • Gastrointestinal Agent
  • Histamine H1 Antagonist
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Serotonin Antagonist
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidineChEBI
1-Methyl-4-(5H-dibenzo(a,D)cycloheptenylidene)piperidineChEBI
4-(5-Dibenzo(a,D)cyclohepten-5-ylidine)-1-methylpiperidineChEBI
4-(5H-Dibenzo(a,D)cyclohepten-5-ylidene)-1-methylpiperidineChEBI
4-Dibenzo[a,D]cyclohepten-5-ylidene-1-methyl-piperidineChEBI
5-(1-Methylpiperidylidene-4)-5H-dibenzo(a,D)cyclophepteneChEBI
CiproheptadinaChEBI
CyproheptadinumChEBI
CiprovitKegg
AnterganHMDB
PeriactinHMDB
PeritolHMDB
ViternumHMDB
DihexazinHMDB
Chemical FormulaC21H21N
Average Molecular Mass287.398 g/mol
Monoisotopic Mass287.167 g/mol
CAS Registry Number129-03-3
IUPAC Name1-methyl-4-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}piperidine
Traditional Nameperiactin
SMILESCN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12
InChI IdentifierInChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
InChI KeyJJCFRYNCJDLXIK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point112.3-113.3°C
Boiling PointNot Available
SolubilitySoluble
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP5.02ALOGPS
logP4.38ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)8.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity105.17 m³·mol⁻¹ChemAxon
Polarizability34.17 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-1090000000-7d19fca2a65a93c449d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0290000000-964629904e89d79568d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0290000000-964629904e89d79568d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000m-6790000000-4e9938638118593eb406Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1090000000-3117ec5d9639f751f7b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3290000000-2935111fa6fa07111de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00r6-9370000000-df84a6a14decead8dedfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-78685e74ff4bff75d39bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-cb222eada7f0bf316df6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022i-5190000000-4e162fb598e8db9d6e77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-107477c8d28ce3506c90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-c2a155a089dd265a5433Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-4190000000-eaa52ca5faae687ab50fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-26c7f893d45bf33544e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-2c051f1f630ec47ecb1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0090000000-012e0121acf874e7bd11Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kr-2290000000-a17c27a9f171b058f2c3Spectrum
Toxicity Profile
Route of ExposureWell absorbed after oral administration.
Mechanism of ToxicityCyproheptadine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Cyproheptadine also competes with serotonin at receptor sites in smooth muscle in the intestines and other locations. Antagonism of serotonin on the appetite center of the hypothalamus may account for Cyproheptadine's ability to stimulate appetite.
MetabolismHepatic (cytochrome P-450 system) and some renal. Route of Elimination: After a single 4 mg oral dose of14C-labelled cyproheptadine HCl in normal subjects, given as tablets 2% to 20% of the radioactivity was excreted in the stools. At least 40% of the administered radioactivity was excreted in the urine.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as an antihistaminic/anticholinergic and antiserotonergic agent. For treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, allergic conjunctivitis due to inhalant allergens and foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, cold urticaria, dermatographism, and as therapy for anaphylactic reactions adjunctive to epinephrine.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsDrowsiness, epigastric distress (dysphagia), nausea, vomiting, (it is noted that these side effects are much more common in people with neuromuscular disorders). [Wikipedia]
TreatmentIf vomiting has not occurred spontaneously the patient should be induced to vomit with syrup of ipecac. If the patient is unable to vomit, perform gastric lavage followed by activated charcoal. Isotonic or 1/2 isotonic saline is the lavage of choice. Precautions against aspiration must be taken especially in infants and children. When life threatening CNS signs and symptoms are present, intravenous physostigmine salicylate may be considered. Dosage and frequency of administration are dependent on age, clinical response, and recurrence after response. (See package circulars for physostigmine products.) Saline cathartics, as milk of magnesia, by osmosis draw water into the bowel and, therefore, are valuable for their action in rapid dilution of bowel content. Stimulants should not be used. Vasopressors may be used to treat hypotension. (3)
Concentrations
Not Available
DrugBank IDDB00434
HMDB IDHMDB0014578
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCyproheptadine
Chemspider ID2810
ChEBI ID4046
PubChem Compound ID2913
Kegg Compound IDC06935
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Engelhardt, E.L.; U S . Patent 3,014,911; December 26, 1961; assigned to Merck & Co., Inc.

MSDSLink
General References
1. Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10843226